Manufacture of synthetic thymol



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MANUFACTURE OF SYNTHETIC THYMUL.

No Drawing.

Application filed February 25, ieae. serial no. 539,279.

(FEET-3D UHDEE THE AQT 01' IZARGEIB, 1883, 22 STAT. 1L., 625.)

To all whom it may concern:

Be it known that 1, MAX PHILLIPS, a citizcn of the United States,'and anemplo cc of the Department of Agriculture of the nlted 5 States ofAmerica, residing in the city of Evansville, county of Rock, State ofWisconsin, whose post-oflice address is care of Department ofAgriculture, Washington, D. C",

have invented certain new'and useful Imin provements in the Manufactureof Synthetic vThymol, of which the following is a specification.

This application is made under the act of March 3, 1883, chaper 14:3 (22Stat, 625) 115 and the invention herein described and claimed ma be usedby the Government vof the United tates or any of its oilicers or emloyees in the prosecution of work for the overent, or any personin theUnited States, without payment to me of any royalty thereon.

The present invention relates to the production of thymol from cymidinesulphonic acid, l-methyl 2-amino-3 or 5-sulphonic-d- I p been added, isheated to boiling and acidified 25 isoKropyl-benzene.

. ccording to U. S. Patent No. 1,332,680, cymidine sulphonic acid isfirst diazotized, the diazo cymene sulphonic acid reduced with tinchloride, or with formic acidand 3e powdered copper, and thecymene-3-sulphonic acid thus obtained fused with sodium hydroxide andthymol obtained. T have found that the conversion of cymidine sulphonicacid into thymol can best be accomplished by diazotizing the cymidinesula -phonic acid, reducing the diazo cymene sulphonic acid with astrong sodium bisulphite solution, acidifying such solution withhydrochloric acid, getting cymyl hydrazine-3 4a or, 5-sulphonic acid;then treat 1| the hydrazine compound with copper sulp ate or, ferricchloride solution, whereupon the hydrazlne group is completel removedand cymene-B-sulphonic acid H =1) is obtained. The sodium salt of thissulphonic acid when fused with either sodium orpotassium hydroxides isconverted into thymol.

The process of converting cymidine sulphonic acid into thymol ispreferably carried out as follows: 23 parts of cymidine sulphonic acidis added to 100 parts of water and 5.5 parts sodium carbonate added.Twenty-five parts concentrated hydrochloric acid (sp. gr. 1.19) or 10parts concentrated sulphuric acid (sp. gr. 1.84) is added in a finestream and suspension thus obtained, cooled to about 5 C. and diazotizedwith sodium nitrite solution in the usual manner. The diazocymenesulphonic acid thus obtained is added to a cold sodium bisulphitesolution, prepared by adding 30 parts sodium sulphite in 200 partsofwater and saturating the solution withsulphur dioxide gas. The sodiumbisulphite solution to which the diazo cymene sulphonic acid had 65 withhydrochloric acid.v On concentrating and cooling the solution, cymylhydrazine copper is deposited, which may be filtered 0d. The filtrate isneutralized with lime and the calcium salt of cymene-3-sulphonic acid(Cl-ll =1) then. converted into the sodium salt bymeans of sodiumcarbonate. The sodium cymene sulphonate when fused with either sodium orpotassium hydroxides is a converted into thol. I

eliminating the hydrazine group with cop-- per sulphate,obtaining'cymene 3-sulphonic acid and fusin the sodium salt of cymene-3-suiphonic aci with sodium hydroxide.

2. The process of making thymol, compris-- ing the diazotization ofcymidine sulphonic The reactions which take place in the process. areconven iently;represented as follows: p I

acid, reducing the diazo cymene sulphonic acid with sodium bisulphitesolution to cymyl hydrazine 3 or 5-sulphonic acid, eliminating thehydrazine group with ferric chloride solution, obtaining cymene3-sulphon1c acid,

and fusing the sodium salt of cymene-3-sulphonicacid with potassiumhydroxide.

In testimony whereof I aflix my signature in the presence of twosubscribing witnesses.

MAX PHILLIPS.

Witnesses MARSHALL J. Gose, GERALD H. Mame.

